Synthesis of benzoheterocycles by palladium-catalyzed migratory cyclization through an unexpected reaction cascade

Wen-Cong Li, Lin Zhang, Shiming Bai, Jia-Hao Zhao, Guang-Rui Liu, Yu Lan (), Shufeng Chen () and Jialin Ming ()
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Wen-Cong Li: Inner Mongolia University
Lin Zhang: Chongqing University
Shiming Bai: Inner Mongolia Academy of Science and Technology
Jia-Hao Zhao: Inner Mongolia University
Guang-Rui Liu: Inner Mongolia University
Yu Lan: Chongqing University
Shufeng Chen: Inner Mongolia University
Jialin Ming: Inner Mongolia University

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract Migratory functionalization of C–H bonds through metal migration from carbon to carbon under transition metal catalysis is a process of significant academic and industrial interest. Herein, a palladium-catalyzed migratory cyclization of α-bromoalkene derivatives ArXCBr=CH2, in which X denotes a phosphorus (P(O)R), silicon (SiR2), sulfur (SO2), carbon (C(O)), nitrogen (NTs), or oxygen-based moiety, affording various benzoheterocyclic compounds has been developed. Mechanistic investigations have demonstrated that the cyclization reaction proceeds through an unexpected cascade, with trans-1,2-palladium migration between sp2 carbons being a key step of catalytic cycle. To the best of our knowledge, this type of metal migration has not been reported previously.

Date: 2025
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DOI: 10.1038/s41467-025-58633-5

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